Hexane → HCID 59501395, compound

Participants

Reaction Conditions

Reaction Steps

In a 500 mL three-necked flask was placed 5.0 g (17 mmol) of 2-(4-bromophenyl)-5-phenyl-1,3,4-oxadiazole, and the atmosphere in the flask was replaced with nitrogen. Then, 100 mL of tetrahydrofuran (abbreviation: THF) was added to this mixture. This solution was cooled to −78° C., followed by addition of 13 mL (20 mmol) of a 1.5 mol/L hexane solution of n-butyllithium. This mixture was stirred under a nitrogen stream at −78° C. for 2 hours. Then, a solution in which 2.0 g (7.6 mmol) of 2-tert-butylanthraquinone was dissolved in tetrahydrofuran was added to this mixture a little at a time. This mixture was stirred at room temperature for 24 hours. Then, water was added to the reaction solution and the resulting mixture was stirred, followed by separation of the organic layer from the aqueous layer. The organic layer and the extract were combined and washed with saturated brine, and then the organic layer was dried with magnesium sulfate. Then, this mixture was suction filtered, and the resulting filtrate was concentrated to give a brown oily substance.

Provenance & Evidence